Process for the preparation of a hydrogenated polymer

ABSTRACT

This invention relates to a process for the preparation of a hydrogenated polymer comprising the steps of hydrogenation of at least one carbon-carbon double bond of an unsaturated polymer in latex in the presence of hydrazine, an oxidizing compound and a catalyst, followed by separation of the hydrogenated polymer from the latex. After the separation of the hydrogenerated polymer from the latex a mixing step is carried out in which the hydrogenated polymer is first mixed with an amine group containing compound and next the hydrogenated polymer is mixed with a compound that is capable of reacting with an amine. The invention also relates to the hydrogenated polymer. The invention further relates to the use of this polymer in a compounds to make an article by shaping and vulcanisation

The present invention relates to a process for the preparation of ahydrogenated polymer comprising the steps of hydrogenation of at leastone carbon-carbon double bond of an unsaturated polymer in latex in thepresence of hydrazine, an oxidizing compound and a catalyst, followed byseparation of the hydrogenated polymer from the latex. The inventionalso relates to the hydrogenated polymer. The invention further relatesto the use of this polymer in a compound to make an article.

A process for the preparation of a hydrogenated polymer is disclosed inWO 00/09568. This process comprises the hydrogenation of carbon-carbondouble bonds of an unsaturated polymer in the presence of hydrazine, anoxidizing compound and a catalyst. During the process also an aminecompound is added to improve the processability and to reduce the gelcontent. The amine compound may be added after the hydrogenated polymeris separated from the latex by mixing the amine compound and thehydrogenated polymer in an extruder.

It is a disadvantage of this process that the mechanical properties ofthe hydrogenated polymer are inferior.

It is the object of the present invention to provide a process for thehydrogenation of an unsaturated polymer resulting in improved cureproperties and in a polymer having improved mechanical properties.

The process according to the invention is characterised in that afterthe separation of the hydrogenated polymer from the latex a mixing stepis carried out in which the hydrogenated polymer is first mixed with anamine group containing compound where after the hydrogenated polymer ismixed with a compound that is capable of reacting with an amine.

The process results in the absence of non-reacted amine residues in thehydrogenated polymer and consequently the cure properties are improved.

Furthermore the mixing of the hydrogenated polymer containing the aminegroup containing compound and the compound that is capable of reactingwith an amine group results in improved mechanical properties forexample improved compression set properties. Said mixing also results inan improved processing of the hydrogenated polymer.

According to a preferred embodiment of the invention the compound thatis capable of reacting with an amine group is a compound according toformula (I):R-Xn  (I)wherein:R is derived from an (cyclo) aliphatic (C₁-C₂₀) group or a (C₆-C₂₀)arylgroupX is a unit derived from an epoxide-, an anhydride-, an isocyanate-, anacid chloride-and/or a carboxylic acid andn=1-5.Preferably n=1-3,

More preferably n=1-2.

Suitable compounds according to formula (I) are for example phthalicacid anhydride, maleic anhydride, acetic anhydride, stearic anhydride,succinic anhydride, cyclohexane dicarboxylic acid anhydride, epoxidisednatural oils for example epoxidised linseed oil, propylene oxide,cyclohexane di-epoxide, stearylchloride, acetyl chloride, toluenediisocyanate, hexane di-isocyanate, phenylene-isocyanate and/or stearicacid.

Preferred compounds are phthalic acid anhydride, maleic anhydride,acetic anhydride, stearic anhydride, tetra hydro phthalic acidanhydride, cyclohexane dicarboxylic acid anhydride, nadic anhydrideand/or succinic anhydride.

More preferably the compound according to formula (I) is phthalic acidanhydride or cyclohexane dicarboxylic acid anhydride.

A suitable unsaturated polymer may for example comprise between 5 and100% by weight of a conjugated diene monomer unit and between 95 and 0%by weight of an ethylenically unsaturated monomer unit.

Suitable examples of conjugated diene monomer units include1,3-butadiene, 2,3-dimethylbutadiene, isoprene and/or 1,3-pentadiene.

The preferred conjugated diene monomer unit is 1,3-butadiene.

Suitable examples of the ethylenically unsaturated monomer units includeunsaturated nitriles for example acrylonitrile and methacrylonitrile,monovinyl aromatic hydrocarbons for example styrene, (o-, m- and p-)alkylstyrene, divinyl aromatic hydrocarbons for example divinylbenzene,dialkenyl aromatics for example diisopropenylbenzene, unsaturatedcarboxylic acids and the esters thereof for example acrylic acid,methacrylic acid, crotonic acid, itaconic acid, maleic acid, methylacrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate and/ormethyl methacrylate.

The preferred ethylenically unsaturated monomer is an unsaturatednitrile and more preferred the ethylenically unsaturated monomer isacrylonitrile.

According to a preferred embodiment of the invention the unsaturatedpolymer is polybutadiene, polyisoprene, styrene-butadiene copolymer(SBR), acrylonitrile-butadiene copolymer (NBR), natural rubber,butadiene-isoprene rubber and/or a terpolymer of butadiene,acrylonitrile and (meth)acrylate acid or ester.

The unsaturated polymer may comprise between 50 and 80% by weight of theconjugated diene-monomer unit and between 20 and 50% by weight of theunsaturated nitrile group-containing monomer unit and more preferablybetween 60 and 70% by weight of the conjugated diene-monomer unit andbetween 30 and 40% by weight of the unsaturated nitrile group-containingmonomer unit.

According to a preferred embodiment of the invention the unsaturatedpolymer is an acrylonitrile-butadiene (NBR) copolymer.

The unsaturated polymer may be prepared by for example an emulsionpolymerisation, a solution polymerisation or a bulk polymerisation.

Preferably, the unsaturated polymer is prepared by means of emulsionpolymerisation in water and the obtained unsaturated polymer becomesavailable in latex form. U.S. Pat. No. 5,442,009 discloses a suitableprocess for the preparation of the unsaturated polymer in latex.

If the unsaturated polymer is not available as a latex, the unsaturatedpolymer is preferably dispersed into an aqueous phase.

The latex comprising the unsaturated polymer may be hydrogenated assuch. The polymer content of the latex may range between 1 and 70 wt. %,and preferably between 5 and 40 wt. %.

Preferred amine group containing compounds are amines according toformula (II):X—R—Y  (II)wherein:R is derived from an aliphatic group comprising at least one C atom orderived from an aromatic group comprising at least 6 C-atoms,X is a hydrogen atom, NH₂—, OH— or SH-group andY is a NH₂—, OH— or SH-group.

A preferred compound is a compound according to formula (III)NH₂—R—X  (III)

Suitable examples of compounds according to formula (III) aremethylamine, ethylamine, ethylene diamine, dodecylamine, methanolamine,ethanolamine, cyclohexyldiamine, o-phenylene diamine, 3,4-toluenediamine, 1,8-naphthalene diamine, aniline, o-aminophenol and/orortho-aminothiobenzene.

Preferably the amine compound is a diamine.

More preferably the amine compound is an ortho-aromatic diamine.

The amount of amine compound may range between for example 0,01 and 5 wt%.

Preferably this amount ranges between 0,1 and 2 wt %.

The hydrazine may be used as such and may be a hydrazine-releasingcompound such as for example hydrazine hydrate, hydrazine acetate,hydrazine sulphate and/or hydrazine hydrochloride. Preferably thehydrazine is hydrazine or hydrazine hydrate.

The hydrazine may be present in a molar ratio between for example 0.1:1and 100:1 (relative to the carbon-carbon double bonds in the polymerchain). Preferably, this ratio ranges between 0.8:1 and 5:1, and thisration most preferably ranges between 0.9:1 and 2:1.

Suitable oxidizing agents are for example air, oxygen, ozone, peroxides,hydrogen peroxide, iodine, iodates and/or hypochlorite.

Preferred oxidizing agents are selected from the group comprising ofperoxides and hydrogen peroxide. Most preferably the oxidizing agent ishydrogen peroxide.

The oxidizing compound is for example added in a molar ratio of between0.1:1 and 100:1 relative to the carbon-carbon double bonds in thepolymer chain. Preferably this ratio ranges between 0.8:1 and 5:1, andmore preferably this ratio ranges between 0.9:1 and 2:1.

The hydrogenation step is carried out in the presence of a catalyst.Suitable catalysts are described in WO 00/09576 and the catalysts arefor example compounds which contain an element from group 13 of thePeriodic Table of the Elements.

Preferably, the catalyst is a compound which contains boron such as forexample a borate, a peroxyborate or boric acid (H₃BO₃).

More preferably the catalyst is boric acid.

Other suitable catalysts are metal salts such as for example disclosedin U.S. Pat. No. 4,452,950. Suitable metal ions are for exampleantimony, arsenic, bismuth, cerium, chromium, cobalt, copper, gold,iron, lead, manganese, mercury, molybdenum, nickel, osmium, palladium,platinum, cerium, silver, tellurium, tin, and/or vanadium.

The preferred metal ions are iron and copper.

Most preferably the metal ion is copper.

Preferably, the oxidizing compound is added to the reaction mixtureafter the addition of the hydrazine.

According to a further preferred embodiment the hydrazine and hydrogenperoxide are added simultaneously to the latex during hydrogenation.

The hydrogenation may be carried out via a batch process and via acontinuous process in closed and in open vessels.

Generally, the hydrogenation reaction temperature ranges between 0° C.and 250° C. Preferably the temperature ranges between 20° C. and 150° C.and more preferably the temperature ranges between 30° C. and 80° C.

Generally, the time of the hydrogenation ranges between for example 1hour and 24 hours. Preferably, this period is less than 12 hours.

After the hydrogenation step the hydrogenated polymer is separated fromthe water phase of the latex. Examples of suitable separation processesare precipitation, latex dewatering via extrusion and steam stripping.

According to a preferred embodiment of the invention the separation steptakes place via precipitation. The precipitation of the hydrogenatedpolymer latex may be carried out for example by the addition of an acidand/or salt to the aqueous dispersion of the hydrogenated polymer, or bythe addition of an alcohol. Preferably a magnesium sulphate-, a calciumchloride- or an aluminium sulphate solution in water is used for theprecipitation.

After the separation of the hydrogenated polymer a mixture comprisinghydrogenated polymer crumb and water is obtained.

The hydrogenated polymer may be dried and the resulting hydrogenatedpolymer crumb may be further processed by for example a mixing stepwhich is carried out after the separation of the hydrogenated polymerfrom the latex.

The mixing step may take place in for example a batch kneader or in acontinuous kneader for example a single, double or multi-screw extruder.

According to a preferred embodiment of the invention the mixing step iscarried out in a double screw extruder. A suitable double screw extrudermay for example comprise a serie of barrels which may be divided inthree zones. The first zone is the melting zone, the second zone is amixing and reaction zone and the third zone is a mixing and reactionzone. After the third zone vacuum may be applied to remove all or a partof the injected compounds and/or solvents.

In the first zone the hydrogenated polymer is melted, in the second zonethe amine group containing compound may be injected as a melt orsolution and in the third zone a compound being capable to react withamine groups may be injected for example as a melt or solution into thehydrogenated polymer.

In general, the compound being capable to react with the amine groups isadded after the mixing of the hydrogenated polymer and the aminecompound. Preferably this compound is added after already more than 80%of the amine compound has been reacted with the hydrogenated polymer.The amine content may be determined by for example gas chromatography.

The temperature of the hydrogenated polymer melt in the extruder mayrange for example between 100° C. and 380° C. and preferably between250° C. and 350° C.

It is preferred that oxygen is excluded as much as possible during themixing step and after the hydrogenated polymer has left the extruderstill being hot. To prevent exposure to oxygen cooling under nitrogen orwater may be applied.

During the mixing step a mastication promotor, for examplepentachlorothiophenol or its zinc salt or dibenzamidediphenyl disulfide,may be added to the hydrogenated polymer.

Preferably the mastication promotor is added together with the aminecompound in the second zone.

The present invention also relates to the hydrogenated polymersobtainable by the process of the present invention. The hydrogenatedpolymer of the present invention shows improved mechanical propertiesfor example the stress relaxation properties and the compression setvalues after curing.

The curing of the polymer may be carried out by curing with for examplea sulfur containing curing system, a phenol based curing system and/or aperoxide based curing system.

Examples of suitable sulphur based curing systems are sulphur incombination with thiazole-, mercapto- or sulfenamide compounds ordithiocarbamates with metal oxides for example zinc oxide.

Examples of suitable peroxide curing agents are organic peroxides forexample dicumyl peroxide, di-tert-butylperoxide,2,5-dimethyl-(2,5-di-tert-butylperoxy)hexane,1,3-bis(tert-butylperoxyisopropyl)benzene,1,1-bis(tert-butylperoxy)-2,3,5-trimethylcyclohexane, benzoyl peroxide,2,4-dichlorobenzoyl peroxide, tert-butyl peroxybenzoate, tert-butylperoxyisopropylcarbonate, diacetyl peroxide, lauroyl peroxide,tert-butyl cumyl peroxide or a mixture of any of them.

The hydrogenated polymers according to the present invention may containadditives, such as for instance stabilizers and reinforcing agents.

Suitable stabilizers are for example free radical stabilizers,antioxidants, dihydroquinoline derivatives, benzimidazole derivativesand/or naphthylamine derivatives. Suitable examples are described in theRubber Technology Handbook, author Werner Hofmann, Carl Hanser Verlag,Munich, Vienna, New York, 1989 at pages 264-268.

Examples of suitable reinforcing agents are carbon black and silica.

The additives may for example be added to the unsaturated polymer beforethe start of the hydrogenation, the additives may be added before theseparation of the hydrogenated polymer. It is also possible to add theadditives during the mixing step.

The compounds used for the production of the articles are produced bymixing the hydrogenated nitrile rubber obtained with the processaccording to the invention with rubber compounding agents such as forexample fillers, reinforcing agents, plasticisers, anti-oxidants and/orvulcanisation agents in a mixing process.

The articles are made using the compounds which are shaped by extrusionor moulding and cured (vulcanized) by heating the shaped products in amould or by heating the extrudate during a certain period of time. Anarticle based on the products obtained with the process according to theinvention is resistant to oil, heat and chemicals. The article may beapplied in many technical fields such as for example automotiveindustry, oil industry, electrical industry, engineering industry, shipbuilding industry, household machines, paper manufacturing industry andcable industry.

A preferred technical field is the automotive industry.

Examples of articles in the automotive industry are heat resistantautomotive parts for example belts, boots, hoses and seals. Thesearticles may be synchronous belts, power transmission, hoses, seals,gaskets, boots and bellows. Specific examples are toothed timing belts,(poly) V-belts, multi-ribbed belts, fuel hoses, air conditioning hoses,radiator hoses, heater hoses, turbo charge hoses, constant velocityjoint boots and propellor shaft boots and vibration dampers. Otherautomotive applications include for example cylinder head O-rings, chaintensioners guides, water pump seals, transmission seals and camshaftabsorbers.

Examples of applications in the oil well industry are control lineprotectors, oil well packers, drill pipe protectors, rotary hose, pumpstators, blow out preventors and gaskets.

Examples of applications in the cable industry are military cables andmarine cables.

Examples of applications in industrial machines are conveyer belts, heatexchanger membranes, heat exchanger gaskets, O-rings and pump stators.

Examples of applications in aircraft are helicopter blade couplingsystem, seals, gaskets and rollers for airplane holds.

In paper manufacturing hard roll covers and roll coverings may be basedon the products according to the invention.

The articles may be reinforced with fibers. Suitable fibers are forexample synthetic fibers such as for example nylon 6, nylon 66, nylon46, polyester, rayon, aromatic polyamide fibers, glass fibers, steelfibers and/or carbon fibers.

These fibers may have a treatment to improve bonding with thehydrogenated polymer. An example of this treatment is a dip of a rubberlatex containing a condensate of a resorcinol formaldehyde resin. Therubber latex may be for example a butadiene-vinylpyridine latex, ahydrogenated nitrile latex, an acrylonitrile-butadiene-(meth)acrylicacid latex and/or a acrylonitrile-butadiene latex. Generally glassfibers have an additional treatment before the latex treatment such asfor example a treatment with a silane compound for example epoxysilaneand aminosilane.

The (pretreated) fibers are combined with the rubber compound inaccordance with usual methods for producing for example belts, hoses andthe desired articles.

After having given the rubber compound the desired shape thevulcanisation is performed.

The polymer obtained with the process according to the invention mayalso be applied in thermoplastic and in thermosetting compositions suchas for example in thermoplastics as reinforcement in blends with PVC, asmodifier in blends with engineering thermoplastics, use in powder form,increasing oil resistance, heat resistance and impact strength and inthermosetting compositions the product may be used with for example EPDMand an acrylate. The polymer may also be applied as a plasticizer.

The process according to the present invention will be elucidated in thefollowing experiments and examples, without being restricted thereto.

EXPERIMENT A

The Mixing of a Hydrogenated Polymer with an Amine Group ContainingCompound

The hydrogenation of NBR was performed in a 2000 liter reactor equippedwith stirrer, nitrogen outlet and cooling jacket.

Boric acid (9,3 kg), water (10 kg) and hydrazine 85% hydrate (72,11 kg)were charged into the reactor. After the boric acid was dissolved 380 kgof NBR latex containing 25 wt % solids was charged. The NBR had a boundacrylonitrile of 33 wt % and a Mooney of 30 (ML 1+4) at 100° C.

The hydrogenation was started under stirring with the addition ofhydrogen peroxide (35 wt % in water) and lasted for 12 hrs. The additionof hydrogen peroxide was stopped when the residual hydrazine level was<5 ppm. During the hydrogenation the temperature was kept on 45° C.

The HNBR latex was coagulated in a stirred coagulation vessel by theaddition of a concentrated calcium chloride solution and the wet HNBRrubber was dried in an oven at 60-70° C.

The dried HNBR was mixed with 2 wt % 3,4-toluene diamine (TDA) on a 3liter Farrell batch kneader with a maximum temperature of 90° C.

The resulting HNBR-TDA mixture was fed into a ZSK 30 extruder UD 39consisting out of 14 barrels. Temperature set over the extruder was 275°C., screw speed was 250 rpm and throughput was 6 kg/h.

The extrudate was cooled in a water-bath.

EXAMPLE I

The Mixing of the Hydrogenated Polymer with a Compound that is Capableof Reacting with an Amine Group

Experiment A was repeated and after the cooling in a water-bath the theextruded HNBR was mixed with 2 wt % phthalic anhydride on a 3 literFarrel kneader.

EXAMPLE II AND COMPARATIVE EXAMPLE A

The HNBR obtained according to Experiment A and the HNBR obtainedaccording to Example I were mixed with the components according to TableI. (the amounts are given in parts per hundred) to obtain masterbatches.

The mixing equipment was an intermeshing Shaw (K1 Intermix Mark IV)laboratory mixer with an empty volume of 5,3 L (batch weight about 3kg). TABLE I Example II A HNBR 100 100 ZnO active 5 5 Stearic acid 1 1Carbon black N-772 40 40 SDPA(N 445) 1 1 ZMMBI 1 1 TOTM 7 7wherein:SDPA(N 445)=styrenated diphenyl amineZMMBI=zinc-2-methylmercaptobenzimidazoleTOTM=trioctyltrimellitate

EXAMPLE III AND COMPARATIVE EXAMPLE B

The processing properties of the masterbatches according to Example IIand according to Comparative Example A were determined with the GarveyDie B test (according to ASTM D 2230-73 with a die area 0,50 cm², ascrew temperature of 80° C. and a zone temperature of 120° C.).

The screw speeds were respectively 30 rpm and 50 rpm as illustrated inTable II in which Comparative Example B shows the results of themasterbatch according to Comparative Example A and Example III shows theresults of the masterbatch according to Example II. TABLE II Example BIII Screw speed (rpm) 30 50 30 50 Head pressure (bar) 53 61 50 56 Power(kW) 1.3 2.3 1.2 2.2 Die swell (%) 98 115 82 60 Output (g/min) 340 599359 619 Appearance Swell and porosity 3 2 3 3 Edge 1 2 3 3The judgment of the appearance was determined visually wherein:4=very good;3=good;2=bad and1=very bad.

The addition of phthalic anhydride improves the die swell properties andthe appearance of the compound based on the hydrogenated polymer.

EXAMPLES IV-V AND COMPARATIVE EXAMPLES C-D

The masterbatches according to Comparative Example B and Example II weremixed with a curing system on a Troester WNU-5 two-roll mill. Thefriction ratio was set at 1:1,2 and the rolls of the mill were cooled.The compounds were stored for at least one day at room temperaturebefore use.

Example IV is directed to the curing of masterbatch II with a sulfurcontaining curing system. The curing took place during 20 minutes at160° C.

Example V is directed to the curing of masterbatch II with a peroxidecontaining curing system. The curing took place during 20 minutes at170° C.

Comparative Example C is directed to the curing of masterbatch B with asulfur containing curing system The curing took place during 20 minutesat 160° C.

Comparative Example D is directed to the curing of masterbatch B with aperoxide containing curing system. The curing took place during 20minutes at 170° C. TABLE III Example IV V C D HNBR 100 100 100 100 ZnOactive 5 5 5 5 Stearic acid 1 1 1 1 Carbon black N-772 40 40 40 40SDPA(N 445) 1 1 1 1 ZMMBI 1 1 1 1 TOTM 7 7 7 7 MBT-80 0.63 — 0.63 —TMTD-80 1.88 — 1.88 — S80 0.63 — 0.63 — Perkadox 14-40 ™ — 6 — 6wherein:SDPA(N 445)=styrenated diphenyl amineZMMBI=methyl-zinc-2-mercaptobenzimidazoleMBT-80=2-mercaptobenzothiazole (80%)TMTD-80=tetramethyl thiuram disulfide (80%)Perkadox 14-40™=peroxide based curing agentTOTM=trioctyltrimellitateS80=sulphur (80%)

The compression set (according to ISO 815 Type B) and the stressrelaxation (according to ISO 3384 Method A) of the products of ExamplesIV-V and Comparative Examples C-D were determined.

The results are given in Table IV and in Table V. TABLE IV C IVCompression set % 22 h/70° C. 40 32 22 h/100° C. 53 48 22 h/150° C. 7267 Stress Relaxation %  24 h 100° C. 65 77  72 h 53 70  168 h 49 64  336h 42 54  672 h 41 49 2016 h 24 40

Table IV shows that the stress relaxation properties and the compressionset properties of sulfur vulcanisates were improved by the addition ofphthalic anhydride. TABLE V D V Hardness IRHD 51 59 Tensile strength Mpa11 20 Compression set % 22 h/−25° C. 99 95 70 h/23° C. 62 38 22 h/70° C.79 39 22 h/100° C. 80 41 22 h/150° C. 82 50

Table V shows that the compression set properties of peroxidevulcanisates were improved by the addition of phthalic anhydride.

1. A process for the preparation of a hydrogenated polymer comprisingthe steps of: hydrogenation of at least one carbon-carbon double bond ofan unsaturated polymer in latex in the presence of hydrazine, anoxidizing compound and a catalyst, followed by separation of thehydrogenated polymer from the latex wherein after the separation of thehydrogenated polymer from the latex a mixing step is carried out inwhich the hydrogenated polymer is first mixed with an amine groupcontaining compound and next the hydrogenated polymer is mixed with acompound that is capable of reacting with an amine.
 2. A processaccording to claim 1 wherein the compound that is capable of reactingwith an amine group is a compound according to formula (I):R—Xn  (I) wherein R is a unit derived from an (cyclo) aliphatic (C₁-C₂₀)group or a (C₆-C₂₀) aryl group, X is a unit derived from an epoxide-, ananhydride-, an isocyanate-, an acid chloride- and/or a carboxylic acidand n=1-5.
 3. A process according to claim 2, wherein the compoundaccording to formula (I) is phthalic acid anhydride, maleic anhydride,acetic anhydride, stearic anhydride, tetra hydro phthalic acidanhydride, cyclohexane dicarboxylic acid anhydride, nadic anhydrideand/or succinic anhydride.
 4. A process according to claim 1, whereinthe unsaturated polymer is polybutadiene, polyisoprene,styrene-butadiene copolymer, acrylonitrile-butadiene copolymer, naturalrubber, butadiene-isoprene rubber and/or a terpolymer of butadiene,acrylonitrile and (meth) acrylate ester or acid.
 5. A process accordingto claim 4, wherein the polymer is acrylonitrile-butadiene copolymer. 6.A process according to claim 1, wherein the amine group containingcompound is an amine according to formula (II):X—R—Y  (II) wherein R is derived from an aliphatic group comprising atleast one C atom or derived from an aromatic group comprising at least 6C-atoms, X is a hydrogen atom, NH₂—, OH— or SH-group and Y is a NH₂—,OH— or SH-group.
 7. A process according to claim 6 wherein the amine isan amine according to formula (III)NH₂—R—X  (III)
 8. A process according to claim 1, wherein the catalystis a compound which contains boron.
 9. A hydrogenated polymer obtainedby the process according to claim
 1. 10. Use of the a polymer obtainedwith the process according to claim 1 in a thermoplastic composition orin a thermosetting composition.
 11. An article based on a polymerobtained with the process according to claim
 1. 12. An article accordingto claim 11 wherein the article is applied in the automotive industry,in the oil industry, in the electrical industry, in the engineeringindustry, in the ship building industry, in household machines, in thepaper manufacturing industry or in the cable industry.
 13. An articleaccording to claim 12 wherein the article is a belt, a hose, a gasket, aboot, a bellow, a vibration damper or a seal.
 14. An article based on apolymer according to claim
 9. 15. A thermoplastic composition comprisinga thermoplastic material and a hydrogenated polymer according to claim9.
 16. A thermosetting composition comprising a thermosetting materialand a hydrogenated polymer according to claim 9.